Buchanan, U.S. Pat. No. 3,530,220, issued Sept. 22, 1970, discloses a class of alkyl 1-carbamoyl-N-(substituted carbamoyloxy)thioformimidates such as methyl 1-(dimethylcarbamoyl)-N-(methylcarbamoyloxy)thioformimidate (oxamyl) which can be represented by the formula ##STR2## The compounds are useful as nematocides, acaricides and insecticides.
Fuchs and Loux, U.S. Pat. No. 3,694,431, issued Sept. 26, 1972, discloses a method of making the compounds of U.S. Pat. No. 3,530,220 which involves nitrosating an acetoacetamide to produce a 2-hydroxyiminoacetoacetamide, e.g. ##STR3## then chlorinating, reacting with a mercaptan, and carbamylating. The 2-hydroxyiminoacetoacetamides are also starting materials for making the substituted 2-hydroxyimino-3-iminobutyramides of the present invention.
Buchanan U.S. Pat. No. 3,557,190, issued Jan. 19, 1971, discloses a method of making the compounds of U.S. Pat. No. 3,530,220 which involves reacting a 2-hydroxyimino ester with two moles of an amine in the presence of water or an alcohol to give the corresponding amide. The amide is then reacted further to give the desired compounds, e.g., ##STR4## This amination procedure also is useful for the conversion of the 3-imino-2-hydroxyiminoacetoacetates and propionylacetates of this invention to the corresponding 2-hydroxyimino-3-iminobutyramides and 2-hydroxyimino-3-iminovaleramides.
Beilstein, Organische Chemie, Vol. III, Fourth Edition, page 745, discloses .alpha.,.beta.-dioximino-butyric acid ethyl ester (A), .alpha.,.beta.-dioximino-butyric acid amide (B), ethyl .alpha.-oximino-acetoacetate phenylhydrazone (C), ethyl .alpha.-acetoximino-acetoacetate (D), and ethyl .alpha.-acetoximino-acetoacetate phenylhydrazone (E), compounds which can be represented by the formulae: ##STR5##
No utility is disclosed for compounds (A)-(E) in the Beilstein reference.